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$96+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in September or August, booked 43 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Portland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$238
(American Airlines)

One-way from

$96
(Priceline)

Popular in

December

Cheapest in

September

Average price

$339

Good round-trip deal

$280 or less

Good one-way deal

$188 or less
From Chicago O'Hare Intl to Portland
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One-way flight from Chicago O'Hare Intl to Portland
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Highest demand for flights based on searches. 17% potential increase in price ($88 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
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Find flight deals from O'Hare Intl to Portland

Cheapest flights from O'Hare Intl to Portland
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Fri 10/313:38 pmPWM - ORD
1 stop6h 32mAmerican Airlines
Deal found 9/15$238
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:50 pmORD - PWM
1 stop7h 09mAmerican Airlines
Sat 11/155:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Deal found 9/15$241
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/188:00 amORD - PWM
1 stop8h 38mAmerican Airlines
Fri 10/247:00 amPWM - ORD
1 stop9h 58mAmerican Airlines
Deal found 9/17$243
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:45 amORD - PWM
1 stop5h 37mJetBlue
Sat 10/47:09 amPWM - ORD
1 stop12h 14mJetBlue
Deal found 9/15$253
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/121:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
Sun 11/165:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Deal found 9/14$255
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/151:26 pmORD - PWM
2 stops9h 39mDelta
Wed 10/225:42 amPWM - ORD
1 stop5h 29mDelta
Deal found 9/15$256
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/204:02 pmORD - PWM
1 stop6h 39mAmerican Airlines
Mon 11/245:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Deal found 9/17$259
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:30 amORD - PWM
Nonstop2h 26mAmerican Airlines
Mon 11/35:21 pmPWM - ORD
1 stop5h 02mAmerican Airlines
Deal found 9/15$260
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:35 pmORD - PWM
1 stop7h 31mJetBlue
Sat 10/47:09 amPWM - ORD
1 stop12h 14mJetBlue
Deal found 9/15$263

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

O'Hare Intl

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 11/1

5:31 pm-11:17 pm

1 stop4h 46m

Portland

Sat 11/8

4:51 pm-6:52 pm

Nonstop3h 01m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 11/8

8:48 am-2:19 pm

1 stop4h 31m

Portland

Wed 11/12

6:00 am-11:46 am

1 stop6h 46m

$251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/25

7:00 am-1:58 pm

1 stop5h 58m

Portland

Tue 10/28

5:42 am-2:55 pm

2 stops10h 13m

$256

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11/12

6:45 am-4:00 pm

2 stops8h 15m

Portland

Sat 11/15

6:35 am-3:26 pm

2 stops9h 51m

$261

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/15

1:26 pm-12:05 am

2 stops9h 39m

Portland

Wed 10/22

5:42 am-3:00 pm

2 stops10h 18m

$261

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 11/14

5:31 pm-11:17 pm

1 stop4h 46m

Portland

Tue 11/18

4:51 pm-6:52 pm

Nonstop3h 01m

$265

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 3/3

7:30 am-1:51 pm

1 stop5h 21m

Portland

Wed 3/4

6:00 am-10:22 am

1 stop5h 22m

$275

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/4

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

Fri 10/10

6:25 pm-8:25 pm

Nonstop3h 00m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/1

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

Sat 10/4

6:14 am-8:05 am

Nonstop2h 51m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 3/3

5:50 pm-9:14 pm

Nonstop2h 24m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
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Best time to book a flight from O'Hare Intl to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Portland

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Portland. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to PWM?

Find hourly flight availability from O'Hare Intl to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 16% versus a flight in the afternoon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 10 inbound flights from Chicago O'Hare Intl per day. 3 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • How long is the flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Departing from Chicago O'Hare Intl Airport to Portland, Maine will take you 4h 46m. There are 897 mi between Chicago O'Hare Intl Airport and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Portland, Maine round-trip?

    According to our current data, Delta ($163), United Airlines ($228), and American Airlines ($232) offers the cheapest pricing from Chicago O'Hare Intl Airport to Portland, Maine. You may be able to fly from Chicago O'Hare Intl Airport to Portland, Maine for 60% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Portland, Maine?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Portland, Maine are United Airlines (73%), Air New Zealand (71%) and SkyWest Airlines (67%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Portland, Maine?

    While on average a flight from Chicago O'Hare Intl Airport to Portland, Maine is generally $282, our data shows the cheapest flight currently is $129. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $191 for that flight.

  • Can I find deals for flights from O'Hare Intl to Portland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Portland.

  • Can I find deals for business class flights from O'Hare Intl to Portland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top 3 airlines flying from O'Hare Intl to Portland

Discover the top 3 airlines that operate flights from O'Hare Intl to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$385FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$352FlexibilityNo cancel feeOn-time71%

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